Hydrocarbons Question 411

Question: The predominant product formed, when 3-methyl-2-pentene reacts with HOCl, is [IIT-JEE 1995]

Options:

A) $ \underset{CH_3}{\mathop{\underset{|}{\mathop{\overset{ClOH}{\mathop{\overset{||}{\mathop{CH_3-CH_2-C-CH-CH_3}}}}}}}} $

B) $ \underset{CH_3}{\mathop{\underset{|}{\mathop{\overset{ClCl}{\mathop{\overset{||}{\mathop{CH_3-CH_2-C-CH-CH_3}}}}}}}} $

C) $ \underset{CH_3Cl}{\mathop{\underset{||}{\mathop{\overset{OH}{\mathop{\overset{|}{\mathop{CH_3-CH_2-C-CH-CH_3}}}}}}}} $

D) $ \underset{CH_3}{\mathop{\underset{|}{\mathop{\overset{CH_3OH}{\mathop{\overset{||}{\mathop{CH_3-C-CH-CH_3}}}}}}}} $

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Answer:

Correct Answer: C

Solution:

$ CH_3-CH_2-\underset{CH_3}{\mathop{\underset{|}{\mathop{C=}}}}\underset{\underset{{}}{\mathop{}}}{\mathop{CH-CH_3+\overset{-+}{\mathop{HOCl}}}}\to $

$ CH_3-CH_2-\underset{CH_3}{\overset{OH}{\mathop{\underset{|}{\overset{|}{\mathop{C-}}}}}}\overset{\overset{Cl}{\mathop{|}}}{\mathop{CH}}-CH_3 $ Addition takes place according to Markownikoff’s rule in which $ C{l^{+}} $ goes to that carbon atom which is more hydrogenated.